Sulfuric Acid → 4-(6-Fluoro-3,4-dimethoxyphenyl)-7,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline

HRID 1461849노트

반응식

HRID 1461849 반응식
[CH3:1][O:2][C:3]1[C:24]([O:25][CH3:26])=[CH:23][CH:22]=[CH:21][C:4]=1[CH2:5][NH:6][CH2:7][CH:8](O)[C:9]1[C:14]([F:15])=[CH:13][C:12]([O:16][CH3:17])=[C:11]([O:18][CH3:19])[CH:10]=1.S(=O)(=O)(O)O.C([O-])(=O)C.[Na+]>FC(F)(F)C(O)=O>[F:15][C:14]1[C:9]([CH:8]2[C:21]3[C:4](=[C:3]([O:2][CH3:1])[C:24]([O:25][CH3:26])=[CH:23][CH:22]=3)[CH2:5][NH:6][CH2:7]2)=[CH:10][C:11]([O:18][CH3:19])=[C:12]([O:16][CH3:17])[CH:13]=1

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 517045Sodium AcetateHCID 14719568alpha-[[(2,3-Dimethoxybenzyl)amino]methyl]-6-fluoro-3,4-dimethoxybenzyl alcohol

생성물 1

HCID 199597004-(6-Fluoro-3,4-dimethoxyphenyl)-7,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline수율 98.9%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

α-[[(2,3-dimethoxybenzyl)amino]methyl]-6-fluoro-3,4-dimethoxybenzyl alcohol (1.0 g) was dissolved in 7 ml of trifluoroacetic acid, and after adding thereto under ice cooling, conc. sulfuric acid (0.25 ml), the mixture was stirred for 40 minutes. 0.72 g of sodium acetate was added to the reaction mixture, and the mixture was concentrated. To the residue was added chloroform and water, and the mixture was basified by addition of conc. aqueous ammonia under ice cooling. After separating procedure, the chloroform layter was collected, washed with saturated aqueous NaCl solution, and dried over anhydrous sodium sulfate. The solvent was distilled off, 0.94 g of 4-(6-fluoro-3,4-dimethoxyphenyl)-7,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline was obtained as a syrupy matter.

후처리

  1. additionafter adding
  2. concentrationthe mixture was concentrated
  3. additionTo the residue was added chloroform and water
  4. additionthe mixture was basified by addition of conc. aqueous ammonia under ice cooling
  5. customAfter separating procedure
  6. customthe chloroform layter was collected
  7. washwashed with saturated aqueous NaCl solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off

출처 및 근거

ORD 기록
ord-63831087441f42d8a874f289f68bf457
출처 데이터셋
uspto-grants-1991_12
특허 번호
US05077406

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